Sugar-based, environmentally-friendly surfactants for emulsion polymerization

Abstract

A composition for an aqueous emulsion polymerization which comprises at least one derivatized alkyl polyglucoside surfactant in a range of 0.01-10%; water, in a range from 20-80% by weight; at least one monomer for emulsion polymerization making up 20-80% of the emulsion polymerization, and at least one initiator in the range of 0.01-5%; with the derivatized alkylpolyglucosides being polyoxyethylene, ethylene oxide and 1,4-dioxane free.

1 . A composition for an aqueous emulsion polymerization which comprises:
 a. at least one derivatized alkyl polyglucoside surfactant in a range of 0.01-10%;   b. water, in a range from 20-80% by weight;   c. at least one monomer for emulsion polymerization making up 20-80% of the emulsion polymerization   d. at least one initiator in the range of 0.01-5%.   
     
     
         2 . The composition of  claim 1 , wherein the composition is ethylene oxide and 1,4-dioxane free. 
     
     
         3 . The composition of  claim 1 , wherein the monomer for emulsion polymerization is chosen from acrylic acid, methacrylic acid, butyl acrylate, methyl methacrylate, styrene, butadiene, acrylamide, acrylonitrile, ethyl acrylate, vinyl acetate, methyl acrylate, 2-ethylhexyl acrylate, butyl methacrylate, and combinations thereof. 
     
     
         4 . The composition of  claim 1 , wherein the monomer for emulsion polymerization comprises reactive carbon-carbon double bonds. 
     
     
         5 . The composition of  claim 1 , wherein the initiator is chosen from sodium persulfate, ammonium persulfate, potassium persulfate, azo-type initiators, peroxides, and combinations thereof. 
     
     
         6 . The composition of  claim 5 , wherein the peroxide is aqueous hydrogen peroxide 
     
     
         7 . The composition of  claim 5 , wherein the azo-type initiator is chosen from 2,2′-azobis(2-amidinopropane)hydrochloride, 4,4′-azobis-cyanovaleric acid and 2,2′-azobis (2-methylbutaneamidoxime) dihydrochloride tetrahydrate. 
     
     
         8 . The composition of  claim 1 , wherein the derivatized alkyl polyglucoside is chosen from a carboxymethyl derivatized alkyl polyglucoside, a sulfonate derivatized alkyl polyglucoside, a phosphate derivatized alkyl polyglucoside, a sulfosuccinate derivatized alkyl polyglucoside, a glycinate derivatized alkyl polyglucoside, and a citrate derivatized alkyl polyglucoside. 
     
     
         9 . The composition of  claim 1 , wherein the derivatized alkyl polyglucoside is chosen from a polysulfonate derivatized alkyl polyglucoside, polyphosphate derivatized alkyl polyglucoside, polyquaternary derivatized alkyl polyglucoside, polycarboxylated derivatized alkyl polyglucoside, and a polycitrate derivatized alkyl polyglucoside. 
     
     
         10 . The composition of  claim 1 , wherein the derivatized polyglucoside surfactant of the present invention comprises a monosaccharide unit, a disaccharide unit, a linker, and a functionalizing agent. 
     
     
         11 . The composition of  claim 1 , wherein the surfactant is a sodium laurylglucoside hydroxypropylsulfonate surfactant, a sodium decylglucoside hydroxypropylsulfonate surfactant, or a sorbitan oleate decylglucoside cross polymer. 
     
     
         12 . The composition of  claim 1 , wherein the derivatized polyglucoside surfactant of the present invention comprises a monosaccharide unit, a disaccharide unit, a crosslinking agent, and a functionalizing agent. 
     
     
         13 . The composition of  claim 1 , wherein the derivatized alkyl polyglucoside surfactant is a composition that includes the following, as a mixture: 
       
         
           
           
               
               
           
         
         wherein: 
         R is an alkyl chain having 8 to 22 carbon atoms; 
         R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11  are independently selected from the group consisting of: —CH 2 —C(O)—O − M + , or —C(O)CH 2 —C(O)—O − M +   
       
       
         
           
           
               
               
           
         
       
       and H, with the proviso that R 1 -R 11  are not all H;
 R 12  is selected from the group consisting of: 
 —OH, —SO 3   − M + , and —SO 4   −2 M + , —O—P(O)—(OM) 2 , 
 —N(CH 3 ) 2 -R 1A , —O—C(O)—CH 2 —OH(SO 3   − M + )—C(O)—O − M + , 
 
       
         
           
           
               
               
           
         
         R 1A  is CH 3 —(CH 2 ) n —; 
         M is a charge balancing group selected from H, Na, K, or NH 4   + ; and 
         n is an integer from 0-36; 
         and positional isomers thereof. 
       
     
     
         14 . The composition of  claim 1 , wherein the derivatized alkyl polyglucoside surfactant is a composition that includes the following, as a mixture: 
       
         
           
           
               
               
           
         
         wherein: 
         R is an alkyl chain having 8 to 22 carbon atoms; 
         a crosslinking agent of the following formula Cl—CH 2 —CH(OH)—CH 2 —Cl; and 
         a functionalizing agent selected from: 
         (i) 
       
       
         
           
           
               
               
           
         
       
       Cl—CH 2 —CH(OH)—SO 3 M, Cl—CH 2 —CH(OH)—SO 4 M, Cl—CH 2 —CH(OH)—CH 2 —OP(O)—(OM) 2 , and combinations thereof, wherein
 R 1A  is CH 3 (CH 2 ) n —; 
 (ii) —Cl—CH 2 —C(O)—O— − Na + , 2-halocarboxylic acid, α, β-unsaturated carboxylic acid, cyclic carboxylic acid anhydride, and combinations thereof; 
 (iii) 
 
       
         
           
           
               
               
           
         
         M is a charge balancing group selected from H, Na, K, or NH 4   + ; and 
         n is an integer from 0-36; 
         and positional isomers thereof. 
       
     
     
         15 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes the following, as a mixture: 
       
         
           
           
               
               
           
         
         wherein: 
         R is an alkyl chain having 8 to 22 carbon atoms; 
         R 1 , R 2 , R 3 , and R 4  are independently selected from the group consisting of: 
       
       
         
           
           
               
               
           
         
       
       and H, with the proviso that R 1 , R 2 , R 3 , and R 4  are not all H;
 R 12  is selected from the group consisting of: 
 —OH, —SO 3   − M + , —SO 4   −2 M + , and —O—P(O)—(OM) 2 ; 
 M is selected from the group consisting of Na, K, NH 4 ; 
 and 
 
       
         
           
           
               
               
           
         
         wherein 
         R 6 , R 7 , R 8 , R 9 , R 10 , and R 11  are independently selected from the group consisting of: 
       
       
         
           
           
               
               
           
         
       
       and H; and
 R 12  is selected from the group consisting of: 
 —OH, —O—P(O)—(OM) 2 , —SO 3   − M + , and —SO 4   −2 M + , and M is selected from the group consisting of Na, K, NH 4 ; 
 and positional isomers thereof. 
 
     
     
         16 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes the following compound: 
       
         
           
           
               
               
           
         
         wherein APG is alkyl polyglucoside; and positional isomers thereof. 
       
     
     
         17 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes the following compound: 
       
         
           
           
               
               
           
         
         wherein n is between 1 to about 3, and particularly 1.5; 
         R is an alkyl chain; 
         and positional isomers thereof. 
       
     
     
         18 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes the following, as a mixture: 
       
         
           
           
               
               
           
         
         wherein 
         R is alkyl having 8 to 22 carbon atoms; 
         R 1 , R 2 , R 3 , and R 4  are independently selected from 
       
       
         
           
           
               
               
           
         
       
       and H, with the proviso that R 1 , R 2 , R 3 , and R 4  are not all H;
 and 
 
       
         
           
           
               
               
           
         
       
       wherein
 R is alkyl having 8 to 22 carbon atoms; 
 R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11  are independently selected from 
 
       
         
           
           
               
               
           
         
       
       and H, with the proviso that R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11  are not all H;
 and positional isomers thereof. 
 
     
     
         19 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes the following, as a mixture: 
       
         
           
           
               
               
           
         
         wherein; 
         R is alkyl having 8 to 22 carbon atoms; and 
       
       
         
           
           
               
               
           
         
       
       wherein:
 R is alkyl having 8 to 22 carbon atoms; and 
 (c) a sorbitan ester of the following structure: 
 
       
         
           
           
               
               
           
         
         wherein: 
         R 1B  is alkyl having 7 to 21 carbons; 
         a crosslinking agent of the following structure: 
       
       
         
           
           
               
               
           
         
       
       in water; and optionally a functionalizing agent selected from the group of: 
       
         
           
           
               
               
           
         
         Cl—CH 2 —CH(OH)—SO 3 M; 
         Cl—CH 2 —CH(OH)—SO 4 M; 
         Cl—CH 2 —CH(OH)CH 2 —OP(O)—(OM) 2 ; 
         and mixtures thereof; 
         wherein R 1A  is CH 3 —(CH 2 ) n —; 
         n is an integer from 0 to 36; 
         M is a charge balancing group selected from H, Na, K, or NH 4 ; 
         and positional isomers thereof. 
       
     
     
         20 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes the following, as a mixture: 
       
         
           
           
               
               
           
         
         wherein; 
         R is alkyl having 8 to 22 carbon atoms; and 
       
       
         
           
           
               
               
           
         
       
       wherein:
 R is alkyl having 8 to 22 carbon atoms; 
 a crosslinker of the following formula: Cl—CH 2 —CH(OH)—CH 2 —Cl; and 
 a functionalizing agent selected from: 
 
       
         
           
           
               
               
           
         
         Cl—CH 2 —CH(OH)—SO 3 M; 
         Cl—CH 2 —CH(OH)—SO 4 M; 
         Cl—CH 2 —CH(OH)CH 2 —OP(O)—(OM) 2 ; 
         and mixtures thereof; 
         wherein R 1  is CH 3 —(CH 2 ) n —; 
         n is an integer from 0 to 36; 
         M is a charge balancing group selected from H, Na, K, or NH 4 ; 
         and positional isomers thereof. 
       
     
     
         21 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes a compound of the following formula: 
       
         
           
           
               
               
           
         
         wherein R is an alkyl group having from about 8 to about 22 carbon atoms and n is an integer ranging from 4 to 6; and positional isomers thereof. 
       
     
     
         22 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes a compound of the following formula: 
       
         
           
           
               
               
           
         
         wherein R is an alkyl group having from about 8 to about 22 carbon atoms and n is an integer ranging from 4 to 6; and positional isomers thereof. 
       
     
     
         23 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes a compound of the following formula: 
       
         
           
           
               
               
           
         
         wherein R is an alkyl group having from about 8 to about 22 carbon atoms; and positional isomers thereof. 
       
     
     
         24 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes a compound of the following formula: 
       
         
           
           
               
               
           
         
         wherein R 1  is an alkyl group having from about 8 to about 22 carbon atoms, and R 2  is CH 3 (CH 2 ) n , and n is independently an integer from 0-21; and positional isomers thereof. 
       
     
     
         25 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes the following, as a mixture: 
       
         
           
           
               
               
           
         
         wherein 
         R is alkyl having 8 to 22 carbon atoms; 
         R 1 , R 2 , R 3 , and R 4  are independently selected from —CH 2 —CH(OH)—CH 2 —R 12 , and H, with the proviso that R 1 , R 2 , R 3 , and R 4  are not all H; 
         R 12  is —O—C(O)—CH 2 —CH(SO 3 M + )—C(O)—O − M +   
         M is a charge balancing group selected from H, Na, K, or NH 4 , 
         and 
       
       
         
           
           
               
               
           
         
       
       wherein
 R is alkyl having 8 to 22 carbon atoms; 
 R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11  are independently selected from —CH 2 —CH(OH)—CH 2 —R 12 , and H, 
 with the proviso that R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11  are not all H; 
 R 12  is —O—C(O)—CH 2 —CH(SO 3 M + )—C(O)—O − M +   
 M is a charge balancing group selected from H, Na, K, or NH 4 ; 
 and positional isomers thereof. 
 
     
     
         26 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes the following, as a mixture: 
       
         
           
           
               
               
           
         
         wherein one of R 3 , R 4 , R 5 , and R 6  is —CH 2 —C(O)—O − M + or —C(O)—CH 2 —C(O)—O − M + , with the remaining R groups being H; R is alkyl having 6 to 30 carbon atoms; M is H, Na, or K; and 
         (b) a 1,3 dicloloro-2-propanol crosslinker; 
         and positional isomers thereof. 
       
     
     
         27 . The composition of  claim 1 , wherein the functionalized alkyl polyglucoside surfactant is a composition that includes the following, as a mixture: 
       
         
           
           
               
               
           
         
         wherein R is an alkyl having 8 to 22 carbons, and R 2  is: 
       
       
         
           
           
               
               
           
         
         and positional isomers thereof. 
       
     
     
         28 . The composition of  claim 1 , further comprising a co-surfactant. 
     
     
         29 . The composition of  claim 28 , wherein the co-surfactant is a derivatized alkyl polyglucoside surfactant that is ethylene oxide and 1,4-dioxane 
     
     
         30 . A process for producing a latex, comprising:
 providing an aqueous solution that comprises at least one derivatized alkyl polyglucoside surfactant, water, and at least one initiator; and   introducing at least one monomer to the aqueous solution;   wherein the derivatized alkyl polyglucoside is chosen from a carboxymethyl derivatized alkyl polyglucoside, a sulfonate derivatized alkyl polyglucoside, a phosphate derivatized alkyl polyglucoside, a sulfosuccinate derivatized alkyl polyglucoside, a glycinate derivatized alkyl polyglucoside, and a citrate derivatized alkyl polyglucoside.   
     
     
         31 - 33 . (canceled) 
     
     
         34 . A paint composition, comprising:
 an aqueous latex composition comprising:
 at least one derivatized alkyl polyglucoside surfactant; wherein the derivatized alkyl polyglucoside is chosen from a carboxymethyl derivatized alkyl polyglucoside, a sulfonate derivatized alkyl polyglucoside, a phosphate derivatized alkyl polyglucoside, a sulfosuccinate derivatized alkyl polyglucoside, a glycinate derivatized alkyl polyglucoside, and a citrate derivatized alkyl polyglucoside; 
 water; 
 an emulsion polymer; and 
 at least one colorant or pigment. 
   
     
     
         35 . The paint composition of  claim 34 , further comprising at least one of a rheology modifier, solvent, filler minerals, a defoamer, a neutralizing agent, a dispersant, a film formation modifier, a freeze-thaw stabilizer, and a wetting agent, and combinations thereof.